Seminar
Tuesday, April 30, 2019 - 12:00am
Graduate Student Teng Xue will present
"New Advances in Trifluoromethoxylation of Arenes and Heteroarenes via Photoredox Catalysis"
on April 30, 2019 at 4:10pm in Neville Hall, room 3
The trifluoromethoxylation of arenes and heteroarenes is of great importance in organic chemistry, they have been playing a role in the synthesis protocol of fluorine-containing compounds, which contribute tremendous applications to the pharmaceutical and agrochemical industry. Conventionally, approaches towards the preparation of trifluoromethoxylated (OCF3) arenes and heteroarenes are always through transition metal catalysis, which is based on the nucleophilic strategy. Yet, direct and catalytic intermolecular C-H trifluoromethoxylation remains a tricky issue in organic synthesis. Herein, this review summarizes recent breakthrough studies in trifluoromethoxylation reactions. Instead of focusing on the nucleophilic route, groups of Ming-Yu Ngai and Antonio Togni opened a whole new access to the synthesis of trifluoromethoxylated arenes and heteroarenes. They revisited the hitherto neglected radical approach, which occurred through single-electron-transfer (SET) and the radical mechanism mediated by photoredox catalysis. It turned out that the radical trifluoromethoxylation offer an extremely short and mild approach to obviate the need for prefunctionalization of aromatic compounds, which is highly advantaged in the synthesis protocol of taming desired of trifluoromethoxylated arenes and heteroarenes.
References:
1. Weijia Zheng, Cristian A. Morales-Rivera, Johnny W. Lee, Peng Liu, and Ming-Yu Ngai. Angew. Chem. Int. Ed. 2018, 57, 9645-9649.; Angew. Chem. 2018, 130, 9793-9797.
2. Weijia Zheng, Johnny W. Lee, Cristian A. Morales-Rivera, Peng Liu, and Ming-Yu Ngai. Angew. Chem. Int. Ed. 2018, 57, 13795-13799.; Angew. Chem. 2018, 130, 13991-13995
3. Benson J. Jelier, Pascal F. Tripet, Ewa Pietrasiak, Ivan Franzoni, Gunnar Jeschke, and Antonio Togni. Angew. Chem. Int. Ed. 2018, 57, 13784-13789.; Angew. Chem. 2018, 130, 13980-13985.